Herbicidal arylimino-substituted triazoles, thiadiazoles or oxadiazoles

ABSTRACT

The invention relates to new substituted aryliminoheterocycles of the general formula (I) ##STR1## in which A represents oxygen, sulphur or the group N--R 1  where 
     R 1  represents hydrogen or in each case optionally substituted alkyl, alkenyl or akinyl, 
     E represents one of the following groups ##STR2## where Q represents oxygen, sulphur or the group N--R 1  (where R 1  has the abovementioned meaning) and 
     R 2  represents hydrogen, cyano or in each case optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl or cycloalkenyl, 
     R represents hydrogen or in each case optionally substituted alkyl, alkenyl or alkinyl, and 
     Ar represents in each case optionally substituted monocyclic or bicyclic aryl or heteroaryl, 
     to processes for their preparation and to their use as herbicides.

This application is a 371 of PCT/EP95/02547 filed Jun. 30, 1995.

The invention relates to novel substituted aryliminoheterocycles, toprocesses for their preparation and to their use as herbicides.

Substituted aryliminoheterocycles have not been disclosed as yet asbiologically active substances.

There have now been found novel substituted aryliminoheterocycles of thegeneral formula (I) ##STR3## in which A represents oxygen, sulphur orthe group N--R¹ where

R¹ represents hydrogen or in each case optionally substituted alkyl,alkenyl or alkinyl,

E represents one of the following groups ##STR4## where Q representsoxygen, sulphur or the group N--R¹ (where R¹ has the abovementionedmeaning) and

R² represents hydrogen, cyano or in each case optionally substitutedalkyl, alkenyl, alkinyl, cycloalkyl or cycloalkenyl,

R represents hydrogen or in each case optionally substituted alkyl,alkenyl or alkinyl, and

Ar represents in each case optionally substituted monocyclic or bicyclicaryl or heteroaryl.

Thus, the general formula (I) represents the isomeric compounds of thegeneral formulae (IA) and (IB) below. ##STR5##

The novel substituted aryliminoheterocycles of the general formula (I)are obtained when arylimino compounds of the general formula (II)##STR6## in which A, R, R² and Ar have the abovementionedmeanings--and/or compounds which are tautomeric to these--are cyclizedwith reactive carbonic acid derivatives of the general formula (III)##STR7## in which Q has the abovementioned meaning and

X represents halogen, alkoxy, aryloxy or aralkoxy,

if appropriate in the presence of a reaction auxiliary and ifappropriate in the presence of a diluent

and, if appropriate, the resulting compounds of the formulae (IA) and/or(IB), in the event that R² in these formulae represents hydrogen, arereacted with alkylating agents of the general formula (IV)

    R.sup.2 --X.sup.1                                          (IV)

in which

R² has the abovementioned meaning with the exception of hydrogen and

X¹ represents halogen or the group --O--SO₂ --O--R²,

if appropriate in the presence of a reaction auxiliary and ifappropriate in the presence of a diluent.

The novel substituted aryliminoheterocycles of the general formula (I)are distinguished by a powerful herbicidal activity.

In the definitions, the saturated or unsaturated hydrocarbon chains,such as alkyl, alkenyl or alkinyl, are in each case straight-chain orbranched.

Halogen generally represents fluorine, chlorine, bromine or iodine,preferably fluorine, chlorine or bromine, in particular fluorine orchlorine.

The invention preferably relates to compounds of the formula (I) inwhich

A represents oxygen, sulphur or the group N--R¹ where

R¹ represents hydrogen or represents alkyl having 1 to 6 carbon atomswhich is optionally substituted by cyano, halogen, C₁ -C₄ -alkoxy, C₁-C₄ -alkyl-carbonyl or C₁ -C₄ -alkoxy-carbonyl, or represents alkenyl oralkinyl each of which has 2 to 6 carbon atoms and each of which isoptionally substituted by halogen,

E represents one of the following groups ##STR8## where Q representsoxygen, sulphur or the group N--R¹ (where R¹ has the meaning given aboveas being preferred) and

R² represents hydrogen, cyano, or represents alkyl having 1 to 6 carbonatoms which is optionally substituted by cyano, halogen, C₁ -C₄ -alkoxy,C₁ -C₄ -alkyl-carbonyl or C₁ -C₄ -alkoxy-carbonyl, or represents alkenylor alkinyl each of which has 2 to 6 carbon atoms and each of which isoptionally substituted by halogen, or represents cycloalkyl having 3 to6 carbon atoms or cycloalkenyl having 5 or 6 carbon atoms each of whichis optionally substituted by halogen or C₁ -C₄ -alkyl,

R represents hydrogen or represents alkyl having 1 to 6 carbon atomswhich is optionally substituted by cyano, halogen, C₁ -C₄ -alkoxy, C₁-C₄ -alkyl-carbonyl or C₁ -C₄ -alkoxy-carbonyl, or represents alkenyl oralkinyl each of which has 2 to 6 carbon atoms and each of which isoptionally substituted by halogen, and

Ar represents one of the monocyclic or bicyclic aryl or heteroarylgroups below, ##STR9## each of which is optionally substituted, and inwhich R³ represents hydrogen or halogen,

R⁴ represents hydrogen, cyano, nitro, thiocarbamoyl, halogen, or in eachcase optionally halogen-substituted C₁ -C₄ -alkyl or C₁ -C₄ -alkoxy,

R⁵ represents the group below

    --A.sup.1 --A.sup.2 --A.sup.3

in which

A¹ represents a single bond, or represents oxygen, sulphur, --SO--,--SO₂ --, --CO-- or the group --N--A⁴ -- where A⁴ represents hydrogen,hydroxyl, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, phenyl, C₁ -C₄ -alkylsulphonylor phenylsulphonyl or

A¹ furthermore represents C₁ -C₆ -alkanediyl, C₂ -C₆ -alkenediyl, C₂ -C₆-azaalkenediyl, C₂ -C₆ -alkinediyl, C₃ -C₆ -cycloalkanediyl, C₃ -C₆-cycloalkenediyl or phenylene, each of which is optionally substitutedby fluorine, chlorine or bromine,

A² represents a single bond, or represents oxygen, sulphur, --SO--,--SO₂ --, --CO-- or the group --N--A⁴ -- where A⁴ represents hydrogen,hydroxyl, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, phenyl, C₁ -C₄ -alkylsulphonylor phenylsulphonyl or

A² furthermore represents C₁ -C₆ -alkanediyl, C₂ -C₆ -alkenediyl, C₂ -C₆-azaalkenediyl, C₂ -C₆ -alkinediyl, C₃ -C₆ -cycloalkanediyl, C₃ -C₆-cycloalkenediyl or phenylene, each of which is optionally substitutedby fluorine, chlorine or bromine,

A³ represents hydrogen, hydroxyl, amino, cyano, isocyano, thiocyanato,nitro, carboxyl, carbamoyl, thiocarbamoyl, sulpho, chlorosulphonyl,halogen, or represents alkyl, alkoxy, alkylthio, alkylsulphinyl,alkylsulphonyl, alkylamino, dialkylamino, alkoxycarbonyl ordialkoxy(thio)phosphoryl, each of which has 1 to 6 carbon atoms in thealkyl groups and each of which is optionally substituted by halogen orC₁ -C₄ -alkoxy, or represents alkenyl, alkenyloxy, alkenylamino,alkylidenamino, alkenyloxycarbonyl, alkinyl, alkinyloxy, alkinylamino oralkinyloxycarbonyl, each of which has 2 to 6 carbon atoms in thealkenyl, alkylidene or alkinyl groups and each of which is optionallysubstituted by halogen or represents cycloalkyl, cycloalkyloxy,cycloalkylalkyl, cycloalkylalkoxy, cycloalkylidenamino,cycloalkyloxycarbonyl or cycloalkylalkoxycarbonyl, each of which has 3to 6 carbon atoms in the cycloalkyl groups and, if appropriate, 1 to 4carbon atoms in the alkyl groups and each of which is optionallysubstituted by halogen, cyano, carboxyl, C₁ -C₄ -alkyl and/or C₁ -C₄-alkoxycarbonyl, or represents phenyl, phenyloxy, phenyl-C₁ -C₄ -alkyl,phenyl-C₁ -C₄ -alkoxy, phenyloxycarbonyl or phenyl-C₁ -C₄-alkoxycarbonyl, each of which is optionally substituted by nitro,cyano, carboxyl, halogen C₁ -C₄ -alkyl, C₁ -C₄ -halogenoalkyl, C₁ -C₄-alkoxy, C₁ -C₄ -halogenoalkyloxy and/or C₁ -C₄ -alkoxy-carbonyl, (ineach case optionally fully or partially hydrogenated) pyrrolyl,pyrazolyl, imidazolyl, triazolyl, furyl, thienyl, oxazolyl, isoxazolyl,thiazdyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl,pyrimidinyl, triazinyl, pyrazolyl-C₁ -C₄ -alkyl, furyl-C₁ -C₄ -alkyl,thienyl-C₁ -C₄ -alkyl, oxazolyl-C₁ -C₄ -alkyl, isoxazol-C₁ -C₄-alkyl,thiazol-C₁ -C₄ -alkyl,pyridinyl-C₁ -C₄ -alkyl, pyrimidinyl-C₁ -C₄-alkyl, pyrazolylmethoxy, furylmethoxy, or representsperhydropyranylmethoxy or pyridylmethoxy,

R⁶ represents hydrogen or halogen,

R⁷ represents hydrogen, hydroxyl, or represents alkyl having 1 to 6carbon atoms which is optionally substituted by cyano, halogen, C₁ -C₄-alkoxy, C₁ -C₄ -alkyl-carbonyl or C₁ -C₄ -alkoxy-carbonyl, orrepresents alkenyl or alkinyl, each of which has 2 to 6 carbon atoms andeach of which is optionally substituted by halogen, or representscycloalkyl or cycloalkylalkyl, each of which has 3 to 6 carbon atoms inthe cycloalkyl moiety and, if appropriate, 1 to 4 carbon atoms in thealkyl moiety and each of which is optionally substituted by halogen orC₁ -C₄ -alkyl, or represents alkoxy or alkenyloxy, each of which has upto 6 carbon atoms and each of which is optionally substituted byhalogen, or represents benzyl or benzyloxy, each of which is optionallysubstituted by cyano, halogen, C₁ -C₄ -alkyl, C₁ -C₄ -halogenoalkyl, C₁-C₄ -alkoxy or C₁ -C₄ -halogenoalkoxy, and

G represents one of the following groups --O--CO--, --S--CO--,--O--C(R⁸,R⁹)--CO--, --C(R⁸,R⁹)--O--CO--, --C(R⁸,R⁹)--C(R⁸,R⁹)--,--C(R⁸,R⁹)--C(R⁸, R⁹)--CO--, --C(R⁸)═C(R⁸)--, --C(R⁸)═C(R⁸)--CO--,--C(R⁸,R⁹)--CO--, --N(R¹⁰)--C(R⁸,R⁹)--CO--, --C(R⁸)═N--, --O--CO--C(R⁸,R⁹)--

where

R⁸ and R⁹ are identical or different and individually represent hydrogenor alkyl having 1 to 6 carbon atoms or together represent alkanediylhaving 2 to 6 carbon atoms, and

R¹⁰ represents hydrogen or alkyl having 1 to 6 carbon atoms.

In particular, the invention relates to compounds of the formula (I) inwhich

A represents oxygen, sulphur or the group N--R¹ where

R¹ represents hydrogen, or represents methyl, ethyl, n- or i-propyl, n-,i-, s- or t-butyl, each of which is optionally substituted by cyano,fluorine, chlorine, methoxy, ethoxy, acetyl, propionyl, methoxycarbonylor ethoxycarbonyl, or represents propenyl, butenyl, propinyl or butinyl,each of which is optionally substituted by fluorine, chlorine orbromine,

E represents one of the following groups ##STR10## where Q representsoxygen, sulphur or the group N--R¹ (where R¹ has the meaning given aboveas being particularly preferred) and

R² represents hydrogen, cyano, or represents methyl, ethyl, n- ori-propyl, n-, i-, s- or t-butyl, each of which is optionally substitutedby cyano, fluorine, chlorine, methoxy, ethoxy, acetyl, propionyl,methoxycarbonyl or ethoxycarbonyl, or represents propenyl, butenyl,propinyl or butinyl, each of which is optionally substituted byfluorine, chlorine or bromine, or represents cyclopentenyl orcyclohexenyl,

R represents hydrogen, or represents methyl, ethyl, n- or i-propyl, n-,i-, s- or t-butyl, each of which is optionally substituted by cyano,fluorine, chlorine, methoxy, ethoxy, acetyl, propionyl, methoxycarbonylor ethoxycarbonyl, or represents propenyl, butenyl, propinyl or butinyl,each of which is optionally substituted by fluorine, chlorine orbromine, and

Ar represents one of the monocyclic or bicyclic aryl or heteroarylgroups below, ##STR11## each of which is optionally substituted, inwhich

R³ represents hydrogen, fluorine or chlorine,

R⁴ represents hydrogen, cyano, chlorine, bromine, methyl ortrifluoromethyl,

R⁵ represents the group below

    --A.sup.1 --A.sup.2 --A.sup.3

in which

A¹ represents a single bond, or represents oxygen, sulphur, --SO--,--SO₂ --, --CO-- or the group --N--A⁴ -- where A⁴ represents hydrogen,hydroxyl, methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- ori-propoxy, methylsulphonyl or ethylsulphonyl, or

A¹ furthermore represents methylene, ethane- 1,1-diyl, ethane-1,2-diyl,propane-1,1-diyl, propane-1-2-diyl, propane-1-3-diyl, ethene-1,2-diyl,propene-1,2-diyl, propene-1-3-diyl, ethine-1,2-diyl or propine-1-3-diyl,

A² represents a single bond, or represents oxygen, sulphur, --SO--,--SO₂ --, --CO-- or the group --N--A⁴ -- where A⁴ represents hydrogen,hydroxyl, methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- ori-propoxy, methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl orphenylsulphonyl, or

A² furthermore represents methylene, ethane-1,1-diyl, ethane-1,2-diyl,propane-1,1-diyl, propane-1-2-diyl, propane-1-3-diyl, ethene- 1,2-diyl,propene-1,2-diyl, propene-1-3-diyl, ethine-1,2-diyl or propine-1-3-diyl,

A³ represents hydrogen, hydroxyl, amino, cyano, nitro, carboxyl,carbamoyl, sulpho, fluorine, chlorine, bromine, or represents methyl,ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-, i-, s- or t-pentyl,methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, n-, i-, s- ort-pentyloxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- ort-butylthio, methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl,methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl, methylamino,ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino,dimethylamino, diethylamino, methoxycarbonyl, ethoxycarbonyl, n- ori-propoxycarbonyl, dimethoxyphosphoryl, diethoxyphosphoryl,dipropoxyphosphoryl or diisopropoxyphosphoryl, each of which isoptionally substituted by fluorine, chlorine methoxy or ethoxy, orrepresents propenyl, butenyl, propenyloxy, butenyloxy, propenylamino,butenylamino, propylidenamino, butylidenamino, propenyloxycarbonyl,butenyloxycarbonyl, propinyl, butinyl, propinyloxy, butinyloxy,propinylamino, butinylamiino, propinyloxycarbonyl or butinyloxycarbonyl,each of which is optionally substituted by fluorine or chlorine, orrepresents cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl,cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy,cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl,cyclohexylmethyl, cyclopropyl-methoxy, cyclobutylmethoxy,cyclopentylmethoxy, cyclohexylmethoxy, cyclopentylidenamino,cyclohexylidenamino, cyclopentyloxycarbonyl, cyclohexyloxycarbonyl,cyclopentylmethoxycarbonyl or cyclohexyl-methoxycarbonyl, each of whichis optionally substituted by fluorine, chlorine, cyano, carboxyl,methyl, ethyl, n- or i-propyl, methoxycarbonyl or ethoxycarbonyl, orrepresents phenyl, phenyloxy, benzyl, phenylethyl, benzyloxy,phenyloxycarbonyl, benzyloxycarbonyl, (in each case optionally fully orpartially hydrogenated) pyrrolyl, pyrazolyl, imidazolyl, triazolyl,furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl,oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, triazinyl,pyrazolylmethyl, furylmethyl, thienylmethyl, oxazolylmethyl,isoxazolmethyl, thiazolmethyl, pyridinylmethyl, pyrimidinylmethyl,pyrazolylmethoxy, furylmethoxy or pyridylmethoxy, each of which isoptionally substituted by nitro, cyano, carboxyl, fluorine, chlorine,bromine, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy,ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy,methoxycarbonyl and/or ethoxycarbonyl,

R⁶ represents hydrogen, fluorine or chlorine,

R⁷ represents hydrogen, hydroxyl, or represents methyl, ethyl, n- ori-propyl, n-, i-, s- or t-butyl, each of which is optionally substitutedby cyano, fluorine, chlorine, methoxy, ethoxy, acetyl, propionyl,methoxycarbonyl or ethoxycarbonyl, or represents propenyl, butenyl,propinyl or butinyl, each of which is optionally substituted byfluorine, chlorine or bromine, or represents cyclopropyl, cyclobutyl,cyclopentyl, cyclohexyl, cyclopropylmethyl cyclobutylmethyl,cyclopentylmethyl or cyclohexyl-methyl, each of which is optionallysubstituted by fluorine, chlorine, bromine, methyl or ethyl, orrepresents methoxy, ethoxy, n- or i-propoxy, n-, i- or s-butoxy,propenyloxy or butenyloxy, each of which is optionally substituted byfluorine and/or chlorine, or represents benzyl or benzyloxy, each ofwhich is optionally substituted by cyano, fluorine, chlorine, bromine,methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy ortrifluoromethoxy, and

G represents one of the following groups --O--CO--, --S--CO--,--O--C(R⁸,R⁹)--CO--, --C(R⁸,R⁹)--O--CO--, --C(R⁸,R⁹)--C(R⁸,R⁹)--,--C(R⁸)═C(R⁸)--, --C(R⁸,R⁹)--CO--, --N(R¹⁰)--C(R⁸,R⁹)--CO--,--C(R⁸)═N--, O--CO--C(R⁸, R⁹)--

where

R⁸ and R⁹ are identical or different and individually representhydrogen, methyl, ethyl, n- or i-propyl or together representethane-1,2-diyl, and

R¹⁰ represents hydrogen, methyl, ethyl, n- or i-propyl.

The definitions of radicals given above, in general or where preferredranges have been mentioned, apply both to the end products of theformula (I) and, analogously, to the starting materials or intermediatesrequired in each case for the preparation. These definitions of radicalscan be combined with each other as desired, that is to say combinationsbetween the indicated ranges of preferred compounds are also possible.

Examples of the possible combinations of the above-defined groups A, Q,R, R² and Ar are listed below:

    __________________________________________________________________________    A Q R     R.sup.2   Ar                                                        __________________________________________________________________________    S O C.sub.2 H.sub.5                                                                     CH.sub.3                                                                                 ##STR12##                                                S O CH.sub.3                                                                            CH.sub.2 F                                                                               ##STR13##                                                S O C.sub.2 H.sub.5                                                                     CHF.sub.2                                                                                ##STR14##                                                S O CH.sub.3                                                                            CF.sub.3                                                                                 ##STR15##                                                S O CHF.sub.2                                                                           C.sub.2 H.sub.5                                                                          ##STR16##                                                S O CHF.sub.2                                                                           CH.sub.3                                                                                 ##STR17##                                                S O                                                                                ##STR18##                                                                          CHF.sub.2                                                                                ##STR19##                                                S O                                                                                ##STR20##                                                                          CH.sub.3                                                                                 ##STR21##                                                S O CH.sub.3                                                                             ##STR22##                                                                               ##STR23##                                                S O n-C.sub.3 H.sub.7                                                                   CHF.sub.2                                                                                ##STR24##                                                S O n-C.sub.3 H.sub.7                                                                   C.sub.2 H.sub.5                                                                          ##STR25##                                                S O n-C.sub.3 H.sub.7                                                                   CH.sub.3                                                                                 ##STR26##                                                S O C.sub.2 H.sub.5                                                                     CH.sub.2 C CH                                                                            ##STR27##                                                S O C.sub.2 H.sub.5                                                                     CH.sub.2 CHCH.sub.2                                                                      ##STR28##                                                S O C.sub.2 H.sub.5                                                                     CH.sub.2 F                                                                               ##STR29##                                                S O C.sub.2 H.sub.5                                                                     CH.sub.3                                                                                 ##STR30##                                                S O CH.sub.3                                                                            CH.sub.2 F                                                                               ##STR31##                                                S O C.sub.2 H.sub.5                                                                     CHF.sub.2                                                                                ##STR32##                                                S O CH.sub.3                                                                            CF.sub.3                                                                                 ##STR33##                                                S O CHF.sub.2                                                                           C.sub.2 H.sub.5                                                                          ##STR34##                                                S O CHF.sub.2                                                                           CH.sub.3                                                                                 ##STR35##                                                S O                                                                                ##STR36##                                                                          CHF.sub.2                                                                                ##STR37##                                                S O                                                                                ##STR38##                                                                          CH.sub.3                                                                                 ##STR39##                                                S O CH.sub.3                                                                             ##STR40##                                                                               ##STR41##                                                S O n-C.sub.3 H.sub.7                                                                   CHF.sub.2                                                                                ##STR42##                                                S O n-C.sub.3 H.sub.7                                                                   C.sub.2 H.sub.5                                                                          ##STR43##                                                S O n-C.sub.3 H.sub.7                                                                   CH.sub.3                                                                                 ##STR44##                                                S O C.sub.2 H.sub.5                                                                     CH.sub.2 C CH                                                                            ##STR45##                                                S O C.sub.2 H.sub.5                                                                     CH.sub.2 CHCH.sub.2                                                                      ##STR46##                                                S O C.sub.2 H.sub.5                                                                     CH.sub.2 F                                                                               ##STR47##                                                S O C.sub.2 H.sub.5                                                                     CH.sub.3                                                                                 ##STR48##                                                S O CH.sub.3                                                                            CH.sub.2 F                                                                               ##STR49##                                                S O C.sub.2 H.sub.5                                                                     CHF.sub.2                                                                                ##STR50##                                                S O CH.sub.3                                                                            CF.sub.3                                                                                 ##STR51##                                                S O CHF.sub.2                                                                           C.sub.2 H.sub.5                                                                          ##STR52##                                                S O CHF.sub.2                                                                           CH.sub.3                                                                                 ##STR53##                                                S O                                                                                ##STR54##                                                                          CHF.sub.2                                                                                ##STR55##                                                S O                                                                                ##STR56##                                                                          CH.sub.3                                                                                 ##STR57##                                                S O CH.sub.3                                                                             ##STR58##                                                                               ##STR59##                                                S O n-C.sub.3 H.sub.7                                                                   CHF.sub.2                                                                                ##STR60##                                                S O n-C.sub.3 H.sub.7                                                                   C.sub.2 H.sub.5                                                                          ##STR61##                                                S O n-C.sub.3 H.sub.7                                                                   CH.sub.3                                                                                 ##STR62##                                                S O C.sub.2 H.sub.5                                                                     CH.sub.2 C CH                                                                            ##STR63##                                                S O C.sub.2 H.sub.5                                                                     CH.sub.2 CHCH.sub.2                                                                      ##STR64##                                                S O C.sub.2 H.sub.5                                                                     CH.sub.2 F                                                                               ##STR65##                                                S O CH.sub.3                                                                            CH.sub.3                                                                                 ##STR66##                                                S O CH.sub.3                                                                            C.sub.2 H.sub.5                                                                          ##STR67##                                                S O CH.sub.3                                                                            CH.sub.2 CHCH.sub.2                                                                      ##STR68##                                                S O CH.sub.3                                                                            CH.sub.2 C CH                                                                            ##STR69##                                                S O CH.sub.3                                                                            CHF.sub.2                                                                                ##STR70##                                                S O C.sub.2 H.sub.5                                                                     C.sub.2 H.sub.5                                                                          ##STR71##                                                S O CH.sub.3                                                                            CH.sub.2 F                                                                               ##STR72##                                                S O CH.sub.3                                                                            CF.sub.3                                                                                 ##STR73##                                                S O CH.sub.3                                                                            CH.sub.3                                                                                 ##STR74##                                                S O CH.sub.3                                                                            C.sub.2 H.sub.5                                                                          ##STR75##                                                S O CH.sub.3                                                                            CH.sub.2 CHCH.sub.2                                                                      ##STR76##                                                S O CH.sub.3                                                                            CH.sub.2 C CH                                                                            ##STR77##                                                S O CH.sub.3                                                                            CHF.sub.2                                                                                ##STR78##                                                S O C.sub.2 H.sub.5                                                                     C.sub.2 H.sub.5                                                                          ##STR79##                                                S O CH.sub.3                                                                            CH.sub.2 F                                                                               ##STR80##                                                S O CH.sub.3                                                                            CF.sub.3                                                                                 ##STR81##                                                S O CH.sub.3                                                                            CH.sub.3                                                                                 ##STR82##                                                S O CH.sub.3                                                                            C.sub.2 H.sub.5                                                                          ##STR83##                                                S O CH.sub.3                                                                            CH.sub.2 CHCH.sub.2                                                                      ##STR84##                                                S O CH.sub.3                                                                            CH.sub.2 C CH                                                                            ##STR85##                                                S O CH.sub.3                                                                            CHF.sub.2                                                                                ##STR86##                                                S O C.sub.2 H.sub.5                                                                     C.sub.2 H.sub.5                                                                          ##STR87##                                                S O CH.sub.3                                                                            CH.sub.2 F                                                                               ##STR88##                                                S O CH.sub.3                                                                            CF.sub.3                                                                                 ##STR89##                                                S O CH.sub.3                                                                            CH.sub.3                                                                                 ##STR90##                                                S O CH.sub.3                                                                            C.sub.2 H.sub.5                                                                          ##STR91##                                                S O CH.sub.3                                                                            CH.sub.2 CHCH.sub.2                                                                      ##STR92##                                                S O CH.sub.3                                                                            CH.sub.2 C CH                                                                            ##STR93##                                                S O CH.sub.3                                                                            CHF.sub.2                                                                                ##STR94##                                                S O C.sub.2 H.sub.5                                                                     C.sub.2 H.sub.5                                                                          ##STR95##                                                S O CH.sub.3                                                                            CH.sub.2 F                                                                               ##STR96##                                                S O CH.sub.3                                                                            CF.sub.3                                                                                 ##STR97##                                                S O CH.sub.3                                                                            CH.sub.3                                                                                 ##STR98##                                                S O CH.sub.3                                                                            C.sub.2 H.sub.5                                                                          ##STR99##                                                S O CH.sub.3                                                                            CH.sub.2 CHCH.sub.2                                                                      ##STR100##                                               S O CH.sub.3                                                                            CH.sub.2 C CH                                                                            ##STR101##                                               S O CH.sub.3                                                                            CHF.sub.2                                                                                ##STR102##                                               S O C.sub.2 H.sub.5                                                                     C.sub.2 H.sub.5                                                                          ##STR103##                                               S O CH.sub.3                                                                            CH.sub.2 F                                                                               ##STR104##                                               S O CH.sub.3                                                                            CF.sub.3                                                                                 ##STR105##                                               S O CH.sub.3                                                                            CH.sub.3                                                                                 ##STR106##                                               S O CH.sub.3                                                                            C.sub.2 H.sub.5                                                                          ##STR107##                                               S O CH.sub.3                                                                            CH.sub.2 CHCH.sub.2                                                                      ##STR108##                                               S O CH.sub.3                                                                            CH.sub.2 C CH                                                                            ##STR109##                                               S O CH.sub.3                                                                            CHF.sub.2                                                                                ##STR110##                                               S O C.sub.2 H.sub.5                                                                     C.sub.2 H.sub.5                                                                          ##STR111##                                               S O CH.sub.3                                                                            CH.sub.2 F                                                                               ##STR112##                                               S O CH.sub.3                                                                            CF.sub.3                                                                                 ##STR113##                                               S O C.sub.2 H.sub.5                                                                     CH.sub.3                                                                                 ##STR114##                                               S O CH.sub.3                                                                            CH.sub.2 F                                                                               ##STR115##                                               S O C.sub.2 H.sub.5                                                                     CHF.sub.2                                                                                ##STR116##                                               S O CH.sub.3                                                                            CF.sub.3                                                                                 ##STR117##                                               S O CHF.sub.2                                                                           C.sub.2 H.sub.5                                                                          ##STR118##                                               S O CHF.sub.2                                                                           CH.sub.3                                                                                 ##STR119##                                               S O                                                                                ##STR120##                                                                         CHF.sub.2                                                                                ##STR121##                                               S O                                                                                ##STR122##                                                                         CH.sub.3                                                                                 ##STR123##                                               S O CH.sub.3                                                                             ##STR124##                                                                              ##STR125##                                               S O n-C.sub.3 H.sub.7                                                                   CHF.sub.2                                                                                ##STR126##                                               S O n-C.sub.3 H.sub.7                                                                   C.sub.2 H.sub.5                                                                          ##STR127##                                               S O n-C.sub.3 H.sub.7                                                                   CH.sub.3                                                                                 ##STR128##                                               S O C.sub.2 H.sub.5                                                                     CH.sub.2 CH.sub.2 C CH                                                                   ##STR129##                                               S O C.sub.2 H.sub.5                                                                     CH.sub.2 CHCH.sub.2                                                                      ##STR130##                                               S O C.sub.2 H.sub.5                                                                     CH.sub.2 F                                                                               ##STR131##                                               S O C.sub.2 H.sub.5                                                                     CH.sub.3                                                                                 ##STR132##                                               S O CH.sub.3                                                                            CH.sub.2 F                                                                               ##STR133##                                               S O C.sub.2 H.sub.5                                                                     CHF.sub.2                                                                                ##STR134##                                               S O CH.sub.3                                                                            CF.sub.3                                                                                 ##STR135##                                               S O CHF.sub.2                                                                           C.sub.2 H.sub.5                                                                          ##STR136##                                               S O CHF.sub.2                                                                           CH.sub.3                                                                                 ##STR137##                                               S O                                                                                ##STR138##                                                                         CHF.sub.2                                                                                ##STR139##                                               S O                                                                                ##STR140##                                                                         CH.sub.3                                                                                 ##STR141##                                               S O CH.sub.3                                                                             ##STR142##                                                                              ##STR143##                                               S O n-C.sub.3 H.sub.7                                                                   CHF.sub.2                                                                                ##STR144##                                               S O n-C.sub.3 H.sub.7                                                                   C.sub.2 H.sub.5                                                                          ##STR145##                                               S O n-C.sub.3 H.sub.7                                                                   CH.sub.3                                                                                 ##STR146##                                               S O C.sub.2 H.sub.5                                                                     CH.sub.2 C CH                                                                            ##STR147##                                               S O C.sub.2 H.sub.5                                                                     CH.sub.2 CHCH.sub.2                                                                      ##STR148##                                               S O C.sub.2 H.sub.5                                                                     CH.sub.2 F                                                                               ##STR149##                                               S O C.sub.2 H.sub.5                                                                     CH.sub.3                                                                                 ##STR150##                                               S O CH.sub.3                                                                            CH.sub.2 F                                                                               ##STR151##                                               S O C.sub.2 H.sub.5                                                                     CHF.sub.2                                                                                ##STR152##                                               S O CH.sub.3                                                                            CF.sub.3                                                                                 ##STR153##                                               S O CHF.sub.2                                                                           C.sub.2 H.sub.5                                                                          ##STR154##                                               S O CHF.sub.2                                                                           CH.sub.3                                                                                 ##STR155##                                               S O                                                                                ##STR156##                                                                         CHF.sub.2                                                                                ##STR157##                                               S O                                                                                ##STR158##                                                                         CH.sub.3                                                                                 ##STR159##                                               S O CH.sub.3                                                                             ##STR160##                                                                              ##STR161##                                               S O n-C.sub.3 H.sub.7                                                                   CHF.sub.2                                                                                ##STR162##                                               S O n-C.sub.3 H.sub.7                                                                   C.sub.2 H.sub.5                                                                          ##STR163##                                               S O n-C.sub.3 H.sub.7                                                                   CH.sub.3                                                                                 ##STR164##                                               S O C.sub.2 H.sub.5                                                                     CH.sub.2 C CH                                                                            ##STR165##                                               S O C.sub.2 H.sub.5                                                                     CH.sub.2 CHCH.sub.2                                                                      ##STR166##                                               S O C.sub.2 H.sub.5                                                                     CH.sub.2 F                                                                               ##STR167##                                               S O C.sub.2 H.sub.5                                                                     CH.sub.3                                                                                 ##STR168##                                               S O CH.sub.3                                                                            CH.sub.2 F                                                                               ##STR169##                                               S O C.sub.2 H.sub.5                                                                     CHF.sub.2                                                                                ##STR170##                                               S O CH.sub.3                                                                            CF.sub.3                                                                                 ##STR171##                                               S O CHF.sub.2                                                                           C.sub.2 H.sub.5                                                                          ##STR172##                                               S O CHF.sub.2                                                                           CH.sub.3                                                                                 ##STR173##                                               S O                                                                                ##STR174##                                                                         CHF.sub.2                                                                                ##STR175##                                               S O                                                                                ##STR176##                                                                         CH.sub.3                                                                                 ##STR177##                                               S O CH.sub.3                                                                             ##STR178##                                                                              ##STR179##                                               S O n-C.sub.3 H.sub.7                                                                   CHF.sub.2                                                                                ##STR180##                                               S O n-C.sub.3 H.sub.7                                                                   C.sub.2 H.sub.5                                                                          ##STR181##                                               S O n-C.sub.3 H.sub.7                                                                   CH.sub.3                                                                                 ##STR182##                                               S O C.sub.2 H.sub.5                                                                     CH.sub.2 C CH                                                                            ##STR183##                                               S O C.sub.2 H.sub.5                                                                     CH.sub.2 C CH                                                                            ##STR184##                                               S O C.sub.2 H.sub.5                                                                     CH.sub.2 F                                                                               ##STR185##                                               S O C.sub.2 H.sub.5                                                                     CH.sub.3                                                                                 ##STR186##                                               S O CH.sub.3                                                                            CH.sub.2 F                                                                               ##STR187##                                               S O C.sub.2 H.sub.5                                                                     CHF.sub.2                                                                                ##STR188##                                               S O CH.sub.3                                                                            CF.sub.3                                                                                 ##STR189##                                               S O CHF.sub.2                                                                           C.sub.2 H.sub.5                                                                          ##STR190##                                               S O CHF.sub.2                                                                           CH.sub.3                                                                                 ##STR191##                                               S O                                                                                ##STR192##                                                                         CHF.sub.2                                                                                ##STR193##                                               S O                                                                                ##STR194##                                                                         CH.sub.3                                                                                 ##STR195##                                               S O CH.sub.3                                                                             ##STR196##                                                                              ##STR197##                                               S O n-C.sub.3 H.sub.7                                                                   CHF.sub.2                                                                                ##STR198##                                               S O n-C.sub.3 H.sub.7                                                                   C.sub.2 H.sub.5                                                                          ##STR199##                                               S O n-C.sub.3 H.sub.7                                                                   CH.sub.3                                                                                 ##STR200##                                               S O C.sub.2 H.sub.5                                                                     CH.sub.2 C CH                                                                            ##STR201##                                               S O C.sub.2 H.sub.5                                                                     CH.sub.2 C CH                                                                            ##STR202##                                               S O C.sub.2 H.sub.5                                                                     CH.sub.2 F                                                                               ##STR203##                                               S O C.sub.2 H.sub.5                                                                     CH.sub.3                                                                                 ##STR204##                                               S O CH.sub.3                                                                            CH.sub.2 F                                                                               ##STR205##                                               S O C.sub.2 H.sub.5                                                                     CHF.sub.2                                                                                ##STR206##                                               S O CH.sub.3                                                                            CF.sub.3                                                                                 ##STR207##                                               S O CHF.sub.2                                                                           C.sub.2 H.sub.5                                                                          ##STR208##                                               S O CHF.sub.2                                                                           CH.sub.3                                                                                 ##STR209##                                               S O                                                                                ##STR210##                                                                         CHF.sub.2                                                                                ##STR211##                                               S O                                                                                ##STR212##                                                                         CH.sub.3                                                                                 ##STR213##                                               S O CH.sub.3                                                                             ##STR214##                                                                              ##STR215##                                               S O n-C.sub.3 H.sub.7                                                                   CHF.sub.2                                                                                ##STR216##                                               S O n-C.sub.3 H.sub.7                                                                   C.sub.2 H.sub.5                                                                          ##STR217##                                               S O n-C.sub.3 H.sub.7                                                                   CH.sub.3                                                                                 ##STR218##                                               S O C.sub.2 H.sub.5                                                                     CH.sub.2 C CH                                                                            ##STR219##                                               S O C.sub.2 H.sub.5                                                                     CH.sub.2 CHCH.sub.2                                                                      ##STR220##                                               S 0 C.sub.2 H.sub.5                                                                     CH.sub.2 F                                                                               ##STR221##                                               S O C.sub.2 H.sub.5                                                                     CH.sub.3                                                                                 ##STR222##                                               S O CH.sub.3                                                                            CH.sub.2 F                                                                               ##STR223##                                               S O C.sub.2 H.sub.5                                                                     CHF.sub.2                                                                                ##STR224##                                               S O CH.sub.3                                                                            CF.sub.3                                                                                 ##STR225##                                               S O CHF.sub.2                                                                           C.sub.2 H.sub.5                                                                          ##STR226##                                               S O CHF.sub.2                                                                           CH.sub.3                                                                                 ##STR227##                                               S O                                                                                ##STR228##                                                                         CHF.sub.2                                                                                ##STR229##                                               S O                                                                                ##STR230##                                                                         CH.sub.3                                                                                 ##STR231##                                               S O CH.sub.3                                                                             ##STR232##                                                                              ##STR233##                                               S O n-C.sub.3 H.sub.7                                                                   CHF.sub.2                                                                                ##STR234##                                               S O n-C.sub.3 H.sub.7                                                                   C.sub.2 H.sub.5                                                                          ##STR235##                                               S O n-C.sub.3 H.sub.7                                                                   CH.sub.3                                                                                 ##STR236##                                               S O C.sub.2 H.sub.5                                                                     CH.sub.2 C CH                                                                            ##STR237##                                               S O C.sub.2 H.sub.5                                                                     CH.sub.2 C CH                                                                            ##STR238##                                               S O C.sub.2 H.sub.5                                                                     CH.sub.2 F                                                                               ##STR239##                                               S O CH.sub.3                                                                            CH.sub.3                                                                                 ##STR240##                                               S O CH.sub.3                                                                            C.sub.2 H.sub.5                                                                          ##STR241##                                               S O CH.sub.3                                                                            CH.sub.2 CHCH.sub.2                                                                      ##STR242##                                               S O CH.sub.3                                                                            CH.sub.2 C CH                                                                            ##STR243##                                               S O CH.sub.3                                                                            CHF.sub.2                                                                                ##STR244##                                               S O C.sub.2 H.sub.5                                                                     C.sub.2 H.sub.5                                                                          ##STR245##                                               S O CH.sub.3                                                                            CH.sub.2 F                                                                               ##STR246##                                               S O CH.sub.3                                                                            CF.sub.3                                                                                 ##STR247##                                               S O CH.sub.3                                                                            CH.sub.3                                                                                 ##STR248##                                               S O CH.sub.3                                                                            C.sub.2 H.sub.5                                                                          ##STR249##                                               S O CH.sub.3                                                                            CH.sub.2 CHCH.sub.2                                                                      ##STR250##                                               S O CH.sub.3                                                                            CH.sub.2 C CH                                                                            ##STR251##                                               S O CH.sub.3                                                                            CHF.sub.2                                                                                ##STR252##                                               S O C.sub.2 H.sub.5                                                                     C.sub.2 H.sub.5                                                                          ##STR253##                                               S O CH.sub.3                                                                            CH.sub.2 F                                                                               ##STR254##                                               S O CH.sub.3                                                                            CF.sub.3                                                                                 ##STR255##                                               S O CH.sub.3                                                                            CH.sub.3                                                                                 ##STR256##                                               S O CH.sub.3                                                                            C.sub.2 H.sub.5                                                                          ##STR257##                                               S O CH.sub.3                                                                            CH.sub.2 CHCH.sub.2                                                                      ##STR258##                                               S O CH.sub.3                                                                            CH.sub.2 C CH                                                                            ##STR259##                                               S O CH.sub.3                                                                            CHF.sub.2                                                                                ##STR260##                                               S O C.sub.2 H.sub.5                                                                     C.sub.2 H.sub.5                                                                          ##STR261##                                               S O CH.sub.3                                                                            CH.sub.2 F                                                                               ##STR262##                                               S O CH.sub.3                                                                            CF.sub.3                                                                                 ##STR263##                                               S O CH.sub.3                                                                            CH.sub.3                                                                                 ##STR264##                                               S O CH.sub.3                                                                            C.sub.2 H.sub.5                                                                          ##STR265##                                               S O CH.sub.3                                                                            CH.sub.2 CHCH.sub.2                                                                      ##STR266##                                               S O CH.sub.3                                                                            CH.sub.2 C CH                                                                            ##STR267##                                               S O CH.sub.3                                                                            CHF.sub.2                                                                                ##STR268##                                               S O C.sub.2 H.sub.5                                                                     C.sub.2 H.sub.5                                                                          ##STR269##                                               S O CH.sub.3                                                                            CH.sub.2 F                                                                               ##STR270##                                               S O CH.sub.3                                                                            CF.sub.3                                                                                 ##STR271##                                               S O CH.sub.3                                                                            CH.sub.3                                                                                 ##STR272##                                               S O CH.sub.3                                                                            C.sub.2 H.sub.5                                                                          ##STR273##                                               S O CH.sub.3                                                                            CH.sub.2 CHCH.sub.2                                                                      ##STR274##                                               S O CH.sub.3                                                                            CH.sub.2 C CH                                                                            ##STR275##                                               S O CH.sub.3                                                                            CHF.sub.2                                                                                ##STR276##                                               S O C.sub.2 H.sub.5                                                                     C.sub.2 H.sub.5                                                                          ##STR277##                                               S O CH.sub.3                                                                            CH.sub.2 F                                                                               ##STR278##                                               S O CH.sub.3                                                                            CF.sub.3                                                                                 ##STR279##                                               S O CH.sub.3                                                                            CH.sub.3                                                                                 ##STR280##                                               S O CH.sub.3                                                                            C.sub.2 H.sub.5                                                                          ##STR281##                                               S O CH.sub.3                                                                            CH.sub.2 CHCH.sub.2                                                                      ##STR282##                                               S O CH.sub.3                                                                            CH.sub.2 C CH                                                                            ##STR283##                                               S O CH.sub.3                                                                            CHF.sub.2                                                                                ##STR284##                                               S O C.sub.2 H.sub.5                                                                     C.sub.2 H.sub.5                                                                          ##STR285##                                               S O CH.sub.3                                                                            CH.sub.2 F                                                                               ##STR286##                                               S O CH.sub.3                                                                            CF.sub.3                                                                                 ##STR287##                                               S O CH.sub.3                                                                            CH.sub.3                                                                                 ##STR288##                                               S O CH.sub.3                                                                            C.sub.2 H.sub.5                                                                          ##STR289##                                               S O CH.sub.3                                                                            CH.sub.2 CHCH.sub.2                                                                      ##STR290##                                               S O CH.sub.3                                                                            CH.sub.2 C CH                                                                            ##STR291##                                               S O CH.sub.3                                                                            CHF.sub.2                                                                                ##STR292##                                               S O C.sub.2 H.sub.5                                                                     C.sub.2 H.sub.5                                                                          ##STR293##                                               S O CH.sub.3                                                                            CH.sub.2 F                                                                               ##STR294##                                               S O CH.sub.3                                                                            CF.sub.3                                                                                 ##STR295##                                               S O CH.sub.3                                                                            CH.sub.3                                                                                 ##STR296##                                               S O CH.sub.3                                                                            C.sub.2 H.sub.5                                                                          ##STR297##                                               S O CH.sub.3                                                                            CH.sub.2 CHCH.sub.2                                                                      ##STR298##                                               S O CH.sub.3                                                                            CH.sub.2 C CH                                                                            ##STR299##                                               S O CH.sub.3                                                                            CHF.sub.2                                                                                ##STR300##                                               S O C.sub.2 H.sub.5                                                                     C.sub.2 H.sub.5                                                                          ##STR301##                                               S O CH.sub.3                                                                            CH.sub.2 F                                                                               ##STR302##                                               S O CH.sub.3                                                                            CF.sub.3                                                                                 ##STR303##                                               S O CH.sub.3                                                                            CH.sub.3                                                                                 ##STR304##                                               S O CH.sub.3                                                                            C.sub.2 H.sub.5                                                                          ##STR305##                                               S O CH.sub.3                                                                            CH.sub.2 CHCH.sub.2                                                                      ##STR306##                                               S O CH.sub.3                                                                            CH.sub.2 C CH                                                                            ##STR307##                                               S O CH.sub.3                                                                            CHF.sub.2                                                                                ##STR308##                                               S O C.sub.2 H.sub.5                                                                     C.sub.2 H.sub.5                                                                          ##STR309##                                               S O CH.sub.3                                                                            CH.sub.2 F                                                                               ##STR310##                                               S O CH.sub.3                                                                            CF.sub.3                                                                                 ##STR311##                                               S O CH.sub.3                                                                            CH.sub.3                                                                                 ##STR312##                                               S O CH.sub.3                                                                            C.sub.2 H.sub.5                                                                          ##STR313##                                               S O CH.sub.3                                                                            CH.sub.2 CHCH.sub.2                                                                      ##STR314##                                               S O CH.sub.3                                                                            CH.sub.2 C CH                                                                            ##STR315##                                               S O CH.sub.3                                                                            CHF.sub.2                                                                                ##STR316##                                               S O C.sub.2 H.sub.5                                                                     C.sub.2 H.sub.5                                                                          ##STR317##                                               S O CH.sub.3                                                                            CH.sub.2 F                                                                               ##STR318##                                               S O CH.sub.3                                                                            CF.sub.3                                                                                 ##STR319##                                               S O CH.sub.3                                                                            CH.sub.3                                                                                 ##STR320##                                               S O CH.sub.3                                                                            C.sub.2 H.sub.5                                                                          ##STR321##                                               S O CH.sub.3                                                                            CH.sub.2 CHCH.sub.2                                                                      ##STR322##                                               S O CH.sub.3                                                                            CH.sub.2 C CH                                                                            ##STR323##                                               S O CH.sub.3                                                                            CHF.sub.2                                                                                ##STR324##                                               S O C.sub.2 H.sub.5                                                                     C.sub.2 H.sub.5                                                                          ##STR325##                                               S O CH.sub.3                                                                            CH.sub.2 F                                                                               ##STR326##                                               S O CH.sub.3                                                                            CF.sub.3                                                                                 ##STR327##                                               S O CH.sub.3                                                                            CH.sub.3                                                                                 ##STR328##                                               S O CH.sub.3                                                                            C.sub.2 H.sub.5                                                                          ##STR329##                                               S O CH.sub.3                                                                            CH.sub.2 CHCH.sub.2                                                                      ##STR330##                                               S O CH.sub.3                                                                            CH.sub.2 C CH                                                                            ##STR331##                                               S O CH.sub.3                                                                            CHF.sub.2                                                                                ##STR332##                                               S O C.sub.2 H.sub.5                                                                     C.sub.2 H.sub.5                                                                          ##STR333##                                               S O CH.sub.3                                                                            CH.sub.2 F                                                                               ##STR334##                                               S O CH.sub.3                                                                            CF.sub.3                                                                                 ##STR335##                                               S O C.sub.2 H.sub.5                                                                     CH.sub.3                                                                                 ##STR336##                                               S O CH.sub.3                                                                            CH.sub.2 F                                                                               ##STR337##                                               S O C.sub.2 H.sub.5                                                                     CHF.sub.2                                                                                ##STR338##                                               S O CH.sub.3                                                                            CF.sub.3                                                                                 ##STR339##                                               S O CHF.sub.2                                                                           C.sub.2 H.sub.5                                                                          ##STR340##                                               S O CHF.sub.2                                                                           CH.sub.3                                                                                 ##STR341##                                               S O                                                                                ##STR342##                                                                         CHF.sub.2                                                                                ##STR343##                                               S O                                                                                ##STR344##                                                                         CH.sub.3                                                                                 ##STR345##                                               S O CH.sub.3                                                                             ##STR346##                                                                              ##STR347##                                               S O n-C.sub.3 H.sub.7                                                                   CHF.sub.2                                                                                ##STR348##                                               S O n-C.sub.3 H.sub.7                                                                   C.sub.2 H.sub.5                                                                          ##STR349##                                               S O n-C.sub.3 H.sub.7                                                                   CH.sub.3                                                                                 ##STR350##                                               S O C.sub.2 H.sub.5                                                                     CH.sub.2 C CH                                                                            ##STR351##                                               S O C.sub.2 H.sub.5                                                                     CH.sub.2 C CH                                                                            ##STR352##                                               S O C.sub.2 H.sub.5                                                                     CH.sub.2 F                                                                               ##STR353##                                               S O C.sub.2 H.sub.5                                                                     CH.sub.3                                                                                 ##STR354##                                               S O CH.sub.3                                                                            CH.sub.2 F                                                                               ##STR355##                                               S O C.sub.2 H.sub.5                                                                     CHF.sub.2                                                                                ##STR356##                                               S O CH.sub.3                                                                            CF.sub.3                                                                                 ##STR357##                                               S O CHF.sub.2                                                                           C.sub.2 H.sub.5                                                                          ##STR358##                                               S O CHF.sub.2                                                                           CH.sub.3                                                                                 ##STR359##                                               S O                                                                                ##STR360##                                                                         CHF.sub.2                                                                                ##STR361##                                               S O                                                                                ##STR362##                                                                         CH.sub.3                                                                                 ##STR363##                                               S O CH.sub.3                                                                             ##STR364##                                                                              ##STR365##                                               S O n-C.sub.3 H.sub.7                                                                   CHF.sub.2                                                                                ##STR366##                                               S O n-C.sub.3 H.sub.7                                                                   C.sub.2 H.sub.5                                                                          ##STR367##                                               S O n-C.sub.3 H.sub.7                                                                   CH.sub.3                                                                                 ##STR368##                                               S O C.sub.2 H.sub.5                                                                     CH.sub.2 C CH                                                                            ##STR369##                                               S O C.sub.2 H.sub.5                                                                     CH.sub.2 C CH                                                                            ##STR370##                                               S O C.sub.2 H.sub.5                                                                     CH.sub.2 F                                                                               ##STR371##                                               S O CH.sub.3                                                                            CH.sub.3                                                                                 ##STR372##                                               S O CH.sub.3                                                                            C.sub.2 H.sub.5                                                                          ##STR373##                                               S O CH.sub.3                                                                            CH.sub.2 CHCH.sub.2                                                                      ##STR374##                                               S O CH.sub.3                                                                            CH.sub.2 C CH                                                                            ##STR375##                                               S O CH.sub.3                                                                            CHF.sub.2                                                                                ##STR376##                                               S O C.sub.2 H.sub.5                                                                     C.sub.2 H.sub.5                                                                          ##STR377##                                               S O CH.sub.3                                                                            CH.sub.2 F                                                                               ##STR378##                                               S O CH.sub.3                                                                            CF.sub.3                                                                                 ##STR379##                                               S O CH.sub.3                                                                            CH.sub.3                                                                                 ##STR380##                                               S O CH.sub.3                                                                            C.sub.2 H.sub.5                                                                          ##STR381##                                               S O CH.sub.3                                                                            CH.sub.2 CHCH.sub.2                                                                      ##STR382##                                               S O CH.sub.3                                                                            CH.sub.2 C CH                                                                            ##STR383##                                               S O CH.sub.3                                                                            CHF.sub.2                                                                                ##STR384##                                               S O C.sub.2 H.sub.5                                                                     C.sub.2 H.sub.5                                                                          ##STR385##                                               S O CH.sub.3                                                                            CH.sub.2 F                                                                               ##STR386##                                               S O CH.sub.3                                                                            CF.sub.3                                                                                 ##STR387##                                               __________________________________________________________________________

If, for example,4-(4-chloro-2-fluoro-5-methoxy-phenyl)-2-methyl-thio-semicarbazide andphosgene are used as starting materials and chlorodifluoromethane asalkylating agent in the subsequent step, the course of the reaction inthe process according to the invention can be outlined as follows:##STR388##

Formula (II) provides a general definition of the arylimino compounds tobe used as starting materials in the process according to the inventionfor the preparation of the compounds of the general formula (I). Informula (II), A, R, R² and Ar preferably, or in particular, have thosemeanings which have already been mentioned above in connection with thedescription of the compounds of the formula (I) as being preferred, orparticularly preferred, for A, R, R² and Ar.

The starting materials of the formula (II) have been disclosed and/orcan be prepared by known processes (cf. EP-A 258182, U.S. Pat. No.4,721,522, DE-A 3722074, U.S. Pat. No. 5,108,486, preparation examples).

Formula (III) provides a general definition of the reactive carbonicacid derivatives to be furthermore used as starting materials in theprocess according to the invention for the preparation of the compoundsof the general formula (I). In formula (III), Q preferably, or inparticular, has that meaning which has already been mentioned above inconnection with the description of the compounds of the formula (I) asbeing preferred, or particularly preferred, for Q; X preferablyrepresents fluorine, chlorine, bromine, C₁ -C₄ -alkoxy, phenoxy orbenzyloxy, in particular chlorine, methoxy or phenoxy.

The starting materials of the formula (III) are known chemicals forsynthesis.

Formula (IV) provides a general definition of the alkylating agentswhich, if appropriate, are also to be used as starting materials in theprocess according to the invention for the preparation of the compoundsof the general formula (I). In formula (IV), R² preferably, or inparticular, has that meaning which has already been mentioned above inconnection with the description of the compounds of the formula (I) asbeing preferred, or particularly preferred, for R² ; X¹ preferablyrepresents chlorine, bromine, iodine or the group --O--SO₂ --O--R².

The starting materials of the formula (IV) are known chemicals forsynthesis.

Diluents which are suitable for carrying out the process according tothe invention are the customary organic solvents. These include, inparticular, aliphatic, alicyclic or aromatic, optionally halogenatedhydrocarbons, such as, for example, benzine, benzene, toluene, xylene,chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane,dichloromethane, chloroform, tetrachloromethane; ethers, such as diethylether, diisopropyl ether, dioxane, tetrahydrofuran, ethylene glycoldimethyl ether or ethylene glycol diethyl ether; ketones, such asacetone, butanone or methyl isobutyl ketone; nitriles, such asacetonitrile, propionitrile or benzonitrile; amides, such asN,N-dimethylformamide, N,N-dimethylacetamide, N-methylformanilide,N-methyl-pyrrolidone or hexamethylphosphoric triamide; esters, such asmethyl acetate or ethyl acetate, sulphoxides, such as dimethylsulphoxide, alcohols such as methanol, ethanol, n- or i-propanol,ethylene glycol monomethyl ether, ethylene glycol monoethyl ether,diethylene glycol monomethyl ether, diethylene glycol monoethyl ether,mixtures of these with water, or pure water.

The process according to the invention is preferably carried out in thepresence of a suitable reaction auxiliary. The suitable substances areall customary inorganic or organic bases. These include, for example,the hydrides, hydroxides, amides, alcoholates, acetates, carbonates orhydrogen carbonates of alkali metals or alkaline earth metals, such as,for example, lithium hydride, sodium hydride, potassium hydride orcalcium hydride, lithium amide, sodium amide or calcium amide, sodiummethylate or potassium methylate, sodium ethylate or potassium ethylate,sodium propylate or potassium propylate, aluminium isopropylate, sodiumtert-butylate or potassium tert-butylate, sodium hydroxide or potassiumhydroxide, ammonium hydroxide, sodium acetate, potassium acetate orcalcium acetate, ammonium acetate, sodium carbonate, potassium carbonateor calcium carbonate, ammonium carbonate, sodium hydrogen carbonate orpotassium hydrogen carbonate, and basic organic nitrogen compounds, suchas trimethylamine, triethylamine, tripropylamine, tributylamine,ethyl-diisopropylamine, N,N-dimethylcyclohexylamine, dicyclohexylamine,ethyl-dicyclohexylamine, N,N-dimethylaniline, N,N-dimethyl-benzylamine,pyridine, 2-methyl-, 3-methyl- and 4methyl-pyridine, 2,4-dimethyl-,2,6-dimethyl-, 3,4-dimethyl- and 3,5-dimethyl-pyridine,5-ethyl-2-methyl-pyridine, N-methylpiperidine,N,N-dimethylaminopyridine, diazabicyclooctane (DABCO),diazabicyclononene (DBN) or diazabicycloundecene (DBU).

When carrying out the process according to the invention, the reactiontemperatures can be varied within a substantial range. In general, theprocess is carried out at temperatures between -10 C. and +150 C.,preferably at temperatures between 0 C. and 100 C., in particular attemperatures between 10° C. and 80° C. In general, the process accordingto the invention is carried out under atmospheric pressure. However, itis also possible to carry out the process under elevated or reducedpressure, in general between 0.1 bar and 10 bar.

To carry out the process according to the invention, the startingmaterials required in each case are generally employed in approximatelyequimolar amounts. However, it is also possible to use one of the twocomponents employed in each case in a larger excess. In general, thereactions are carried out in a suitable diluent, if appropriate in thepresence of a reaction auxiliary, and the reaction mixture is stirredfor several hours at the temperature required in each case. Working-upin the process according to the invention is carried out in each case bycustomary methods (cf. the preparation examples).

The active compounds according to the invention can be used asdefoliants, desiccants, haulm killers and, especially, as weedkillers.By weeds, in the broadest sense, there are to be understood all plantswhich grow in locations where they are undesired. Whether the substancesaccording to the invention act as total or selective herbicides dependsessentially on the amount used.

The active compounds according to the invention can be used, forexample, in connection with the following plants:

Dicotyledon weeds of the genera: Sinapis, Lepidium, Galium, Stellaria,Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio,Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum,Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippa, Rotala,Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis,Papaver, Centaurea, Trifolium, Ranunculus and Taraxacum.

Dicotyledon crops of the genera: Gossypium, Glycine, Beta, Daucus,Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana,Lycopersicon, Arachis, Brassica, Lactuca, Cucumis and Cucurbita.

Monocotyledon weeds of the genera: Echinochloa, Setaria, Panicum,Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus,Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis,Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea,Dactyloctenium, Agrostis, Alopecurus and Apera.

Monocotyledon crops of the genera: Oryza, Zea, Triticum, Hordeum, Avena,Secale, Sorghum, Panicum, Saccharum, Ananas, Asparagus and Allium.

However, the use of the active compounds according to the invention isin no way restricted to these genera, but also extends in the samemanner to other plants.

Depending on the concentration, the compounds are suitable for totalweed control, for example on industrial terrain and rail tracks, and onpaths and areas with or without tree stands. Equally, the compounds canbe employed for controlling weeds in perennial crops, for exampleforests, ornamental tree plantations, orchards, vineyards, citrusgroves, nut orchards, banana plantations, coffee plantations, teaplantations, rubber plantations, oil palm plantations, cocoaplantations, soft fruit plantations and hopfields, in lawns, turf andpastures, and for selective weed control in annual crops.

The compounds of the formula (I) according to the invention areparticularly suitable for selectively controlling monocotyledon anddicotyledon weeds in monocotyledon and dicotyledon crops, both pre- andpost-emergence.

The active compounds can be converted into the customary formulations,such as solutions, emulsions, wettable powders, suspensions, powders,dusts, pastes, soluble powders, granules, suspoemulsion concentrates,natural and synthetic materials impregnated with active compound, andmicroencapsulations in polymeric substances.

These formulations are produced in a known manner, for example by mixingthe active compounds with extenders, that is liquid solvents and/orsolid carriers, optionally with the use of surfactants, that isemulsifiers and/or dispersants and/or foam-formers.

If water is used as an extender, organic solvents can, for example, alsobe used as auxiliary solvents. Liquid solvents which are mainly suitableare: aromatics such as xylene, toluene or alkylnaphthalenes, chlorinatedaromatics and chlorinated aliphatic hydrocarbons such as chlorobenzenes,chloroethylenes or methylene chloride, aliphatic hydrocarbons such ascyclohexane or paraffins, for example petroleum fractions, mineral andvegetable oils, alcohols such as butanol or glycol as well as theirethers and esters, ketones such as acetone, methyl ethyl ketone, methylisobutyl ketone or cyclohexanone, strongly polar solvents such asdimethylformamide and dimethyl sulphoxide, and water.

Suitable solid carriers are: for example ammonium salts and groundnatural minerals such as kaolins, clays, talc, chalk quartz,attapulgite, montmorillonite or diatomaceous earth, and ground syntheticminerals such as highly disperse silica, alumina and silicates; suitablesolid carriers for granules are: for example crushed and fractionatednatural rocks such as calcite, marble, pumice, sepiolite and dolomite,or else synthetic granules of inorganic and organic meals, and granulesof organic material such as sawdust, coconut shells, maize cobs andtobacco stalks; suitable emulsifiers and/or foam-formers are: forexample non-ionic and anionic emulsifiers, such as polyoxyethylene fattyacid esters, polyoxyethylene fatty alcohol ethers, for example alkylarylpolyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonatesand protein hydrolysates; suitable dispersants are: for examplelignin-sulphite waste liquors and methylcellulose.

Adhesives such as carboxymethylcellulose and natural and syntheticpolymers in the form of powders, granules or latexes such as gum arabic,polyvinyl alcohol and polyvinyl acetate, or else natural phospholipidssuch as cephalins and lecithins, and synthetic phospholipids can be usedin the formulations. Further additives can be mineral and vegetableoils.

It is possible to use colourants such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian Blue, and organic dyestuffs suchas alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs,and trace nutrients such as salts of iron, manganese, boron, copper,cobalt, molybdenum and zinc.

The formulations generally comprise between 0.1 and 95 per cent byweight of active compound, preferably between 0.5 and 90%.

For controlling weeds, the active compounds according to the invention,as such or in the form of their formulations, can also be used asmixtures with known herbicides, ready mixes or tank mixes being possible

Possible components for the mixtures are known herbicides, such as, forexample, anilides, such as, for example, diflufenican and propanil;arylcarboxylic acids, such as, for example, dichloropicolinic acid,dicamba and picloram; aryloxyalkanoic acids, such as, for example, 2,4D, 2,4 DB, 2,4 DP, fluroxypyr, MCPA, MCPP and triclopyr;aryloxy-phenoxy-alkanoic esters, such as, for example, diclofop-methyl,fenoxapropethyl, fluazifop-butyl, haloxyfop-methyl and quizalofop-ethyl;azinones, such as, for example, chloridazon and norflurazon; carbamates,such as, for example, chlorpropham, desmedipham, phenmedipham andpropham; chloracetanilides, such as, for example, alachlor, acetochlor,butachlor, metazachlor, metolachlor, pretilachlor and propachlor;dinitroanilines, such as, for example, oryzalin, pendimethalin andtrifluralin; diphenyl ethers, such as, for example, acifluorfen,bifenox, fluoroglycofen, fomesafen, halosafen, lactofen and oxyfluorfen;ureas, such as, for example, chlortoluron, diuron, fluometuron,isoproturon, linuron and methabenzthiazuron; hydroxylamines, such as,for example, alloxydim, clethodim, cycloxydim, sethoxydim andtralkoxydim; imidazolinones, such as, for example, imazethapyr,imazamethabenz, imazapyr and imazaquin; nitriles, such as, for example,bromoxynil, dichlobenil and ioxynil; oxyacetamides, such as, forexample, mefenacet; sulphonylureas, such as, for example, amidosulfuron,bensulfuron-methyl, chlorimuron-ethyl, chlorsulfuron, cinosulfuron,metsulfuron-methyl, nicosulfuron, primisulfuron, pyrazosulftiron-ethyl,thifensulfuron-methyl, triasulfuron and tribenuron-methyl;thiolcarbamates, such as, for example, butylate, cycloate, diallate,EPTC, esprocarb, molinate, prosulfocarb, thiobencarb and triallate;triazines, such as, for example, atrazine, cyanazine, simazine,simetryn, tertbutryn and terbutylazine; triazinones, such as, forexample, hexazinon, metamitron and metribuzin; others, such as, forexample, aminotriazole, benfuresate, bentazone, cinmethylin, clomazone,clopyralid, difenzoquat, dithiopyr, ethofumesate, fluorochloridone,glufosinate, glyphosate, isoxaben, pyridate, quinchlorac, quinmerac,sulphosate and tridiphane.

Mixtures with other known active compounds such as fungicides,insecticides, acaricides, nematicides, bird repellants, plant nutrientsand soil conditioners, are also possible.

The active compounds can be used as such, in the form of theirformulations or in the use forms prepared therefrom by further dilution,such as ready-to-use solutions, suspensions, emulsions, powders, pastesand granules. They are used in the customary manner, for example bywatering, spraying, atomizing or spreading.

The active compounds according to the invention can be applied eitherbefore or after emergence of the plants. They can also be incorporatedinto the soil before sowing.

The amount of active compound used can vary within a substantial range.It depends essentially on the nature of the desired effect. In general,the rates are between 10 g and 10 kg of active compound per hectare ofsoil surface, preferably between 50 g and 5 kg per ha.

The preparation and use of the active compounds according to theinvention can be seen from the examples which follow.

Preparation Examples EXAMPLE 1 ##STR389##

A suspension of 3.1 g (10 mMol) of2-methyl-4-(7-fluoro-3,4-dihydro-3-oxo-4-propargyl-(2H)-1,4-benzoxazin-6-yl)-thiosemicarbazidein 50 ml of dichloromethane is treated at approximately 20 C. with 6 g(12 mMol) of a 20% strength solution of phosgene in toluene. Thereaction mixture is heated for approximately 15 hours at 40 C., thesolvent is removed in vacuo, and the residue is taken up in water. Themixture is rendered neutral using sodium bicarbonate solution, and thesolid is filtered off, washed with water and dried in vacuo at 40-50 C.

This gives 2.8 g (84% of theory) of2-(7-fluoro-3,4-dihydro-3-oxo-4-propargyl-(2H)-1,4-benzoxazin-6-yl-imino)-3-methyl-3,4-dihydro-5-oxo-(4H)-1,3,4-thiadiazole.Melting point: 214 C.

EXAMPLE 2 ##STR390##

A mixture of 1.7 g (5 mMol) of2-(7-fluoro-3,4-dihydro-3-oxo-4-propargyl-(2H)-1,4-benzoxazin-6yl-imino)-3-methyl-3,4-dihydro-5-oxo-(4H)-1,3,4-thiadiazole,1.4 g (10 mMol) of potassium carbonate and 50 ml of acetonitrile istreated with 1.1 g (7.5 mMol) of methyl iodide. The reaction mixture isheated for 5 hours at 40 C. The solvent is removed in vacuo, the residueis taken up in water, and the mixture is rendered neutral and extractedusing dichloromethane. The organic phase is dried over magnesiumsulphate, concentrated and purified by chromatography (eluent:dichloromethane/methanol: 40:1).

This gives 0.75 g (42% of theory) of3,4-dimethyl-2-(7-fluoro-3,4-dihydro-3-oxo-4-propargyl-(2)-1,4-benzoxazin-6-yl-imino)-3,4-dihydro-5-oxo-1,3,4-thiadiazole.Melting point: 104 C.

EXAMPLE 3 ##STR391##

A solution of 3.3 g (11 mMol) of2-(4-chloro-2-fluoro-5-ethoxy-phenyl-imino)-3-methyl-3,4-dihydro-5-oxo-(4H)-1,3,4-thiadiazolein 80 ml of dimethylformamide is treated with 3.4 g (24 mMol) ofpotassium carbonate, and chlorodifluoromethane is slowly passed in at 60C. in the course of 6 hours. After the reaction has ended, most of thesolvent is removed in vacuo. The oily residue is taken up in water, andthe mixture is rendered neutral using hydrochloric acid and extractedusing dichloromethane. The organic phase is dried over magnesiumsulphate, concentrated and separated by chromatography usingdichloromethane as the eluent.

The first fraction obtained is 0.4 g of2-(4-chloro-2-fluoro-5-ethoxyphenylimino)-4-difluoromethyl-3-methyl-3,4-dihydro-5-oxo-1,3,4-thiadiazole.Melting point: 121 C.

The second fraction obtained is 0.5 g of2-(4-chloro-2-fluoro-5-ethoxyphenylimino)-3-methyl-5-difluoromethoxy-1,3,4-thiadiazole.Melting point: 42 C. ##STR392##

The compound listed as Example 45 in Table 1 can be prepared for exampleas follows: ##STR393##

A solution of 1.7 g (5.7 mMol) of4-(4-cyano-2-fluoro-5-i-propoxy-phenyl)-1,2-dimethylthiosemicarbazide in30 ml of dry dichloromethane is treated with 0.66 g (5.7 mMol) ofthiophosgene. The reaction is slightly exothermic. The reaction mixtureis stirred for 4 hours at reflux temperature, the solvent is removed invacuo, and the residue is stirred with saturated sodium bicarbonatesolution. The solid formed is filtered off with suction, washed withwater and pressed on a porous plate.

This gives 1.5 g (78% of theory) of2-(4-cyano-2-fluoro-5-i-propoxy-phenylimino)-3,4-dimethyl-5-thio-1,3,4-thiadiazoleof melting point 117 C.

Other examples of the compounds of the formula (I)--or of the formulae(1A) and (1B)--which can be prepared analogously to Examples 1 to 3 andfollowing the general description of the preparation process accordingto the invention are those listed in Table 1 below.

                                      TABLE 1                                     __________________________________________________________________________    Examples of the compounds of the formula (I)                                       Gen.                                     Melting point                   Ex. No.                                                                            formula                                                                            Ar               R   R.sup.2  Q  A  (C.)                            __________________________________________________________________________    4    IA                                                                                  ##STR394##      CH.sub.3                                                                          CH.sub.3 O  S  118                             5    IA                                                                                  ##STR395##      CH.sub.3                                                                          C.sub.2 H.sub.5                                                                        O  S   95                             6    IA                                                                                  ##STR396##      CH.sub.3                                                                          CH.sub.3 O  S  103                             7    IA                                                                                  ##STR397##      CH.sub.3                                                                          CN       O  S   60                             8    IA                                                                                  ##STR398##      CH.sub.3                                                                          C.sub.2 H.sub.5                                                                        O  S  117                             9    IA                                                                                  ##STR399##      CH.sub.3                                                                           ##STR400##                                                                            O  S   95                             10   IA                                                                                  ##STR401##      CH.sub.3                                                                          CH.sub.2 CCH                                                                           O  S  147                             11   IA                                                                                  ##STR402##      CH.sub.3                                                                          CH.sub.2 CHCH.sub.2                                                                    O  S  119                             12   IA                                                                                  ##STR403##      CH.sub.3                                                                          CH.sub.3 O  S   72                             13   IA                                                                                  ##STR404##      CH.sub.3                                                                          CH.sub.3 O  S  121                             14   IA                                                                                  ##STR405##      CH.sub.3                                                                          CH.sub.3 O  S   54                             15   IA                                                                                  ##STR406##      CH.sub.3                                                                          CH.sub.3 O  S  156                             16   IA                                                                                  ##STR407##      CH.sub.3                                                                          CH.sub.3 O  S  (oil)                           17   IA                                                                                  ##STR408##      CH.sub.3                                                                          CHF.sub.2                                                                              O  S                                  18   IA                                                                                  ##STR409##      CH.sub.3                                                                          CH.sub.3 O  S  (amorphous)                     19   IA                                                                                  ##STR410##      CH.sub.3                                                                          CH.sub.3 O  S   68                             20   IA                                                                                  ##STR411##      CH.sub.3                                                                          CHF.sub.2                                                                              O  S                                  21   IB                                                                                  ##STR412##      CH.sub.3                                                                          CH.sub.3 O  S   64                             22   IB                                                                                  ##STR413##      CH.sub.3                                                                          CH.sub.3 O  S  105                             23   IA                                                                                  ##STR414##      CH.sub.3                                                                          H        O  S  248                             24   IA                                                                                  ##STR415##      CH.sub.3                                                                          H        O  S  137                             25   IA                                                                                  ##STR416##      CH.sub.3                                                                          H        O  S   67                             26   IA                                                                                  ##STR417##      CH.sub.3                                                                          H        O  S  (oil)                           27   IA                                                                                  ##STR418##      CH.sub.3                                                                          H        O  S  194                             28   IA                                                                                  ##STR419##      CH.sub.3                                                                          H        O  S  (oil)                           29   IA                                                                                  ##STR420##      CH.sub.3                                                                          H        O  S   72                             30   IA                                                                                  ##STR421##      CH.sub.3                                                                          H        O  S  161                             31   IA                                                                                  ##STR422##      CH.sub.3                                                                          H        O  S  115                             32   IA                                                                                  ##STR423##      CH.sub.3                                                                          H        O  S   70                             33   IA                                                                                  ##STR424##      CH.sub.3                                                                          H        O  S  134                             34   IA                                                                                  ##STR425##      CH.sub.3                                                                          H        O  S  158                             35   IA                                                                                  ##STR426##      CH.sub.3                                                                          H        O  S  144                             36   IB                                                                                  ##STR427##      CH.sub.3                                                                          C.sub.2 H.sub.5                                                                        O  S   97                             37   IB                                                                                  ##STR428##      CH.sub.3                                                                          CHF.sub.2                                                                              O  S  119                             38   IA                                                                                  ##STR429##      CH.sub.3                                                                          CH.sub.3 O  S  (amorphous)                     39   IA                                                                                  ##STR430##      CH.sub.3                                                                          CH.sub.3 O  S  125                             40   IA                                                                                  ##STR431##      CH.sub.3                                                                          CH.sub.3 O  S   72                             41   IB                                                                                  ##STR432##      CH.sub.3                                                                          CHF.sub.2                                                                              O  S  (amorphous)                     42   IA                                                                                  ##STR433##      C.sub.2 H.sub.5                                                                   C.sub.2 H.sub.5                                                                        O  S  137                             43   IA                                                                                  ##STR434##      CH.sub.3                                                                          CHF.sub.2                                                                              O  S                                  44   IB                                                                                  ##STR435##      CH.sub.3                                                                          CHF.sub.2                                                                              O  S                                  45   IA                                                                                  ##STR436##      CH.sub.3                                                                          CH.sub.3 S  S  117                             46   IA                                                                                  ##STR437##      CH.sub.3                                                                          CH.sub.3 S  S  233                             47   IA                                                                                  ##STR438##      CH.sub.3                                                                          CH.sub.3 S  S  128                             48   IA                                                                                  ##STR439##      CH.sub.3                                                                          CH.sub.3 S  S  102                             49   IA                                                                                  ##STR440##      CH.sub.3                                                                          CH.sub.3 S  S   90                             50   IA                                                                                  ##STR441##      CH.sub.3                                                                          CH.sub.3 S  S  128                             51   IA                                                                                  ##STR442##      C.sub.2 H.sub.5                                                                   C.sub.2 H.sub.5                                                                        S  S                                  52   IA                                                                                  ##STR443##      CH.sub.3                                                                          CH.sub.3 S  S   61                             53   IA                                                                                  ##STR444##      C.sub.2 H.sub.5                                                                   C.sub.2 H.sub.5                                                                        S  S   67                             54   IA                                                                                  ##STR445##      C.sub.2 H.sub.5                                                                   C.sub.2 H.sub.5                                                                        S  S                                  55   IA                                                                                  ##STR446##      C.sub.2 H.sub.5                                                                   C.sub.2 H.sub.5                                                                        S  S  155                             56   IA                                                                                  ##STR447##      CH.sub.3                                                                          CH.sub.3 S  S   84                             57   IB                                                                                  ##STR448##      CH.sub.3                                                                          CHF.sub.2                                                                              O  S                                  58   IA                                                                                  ##STR449##      CH.sub.3                                                                          CHF.sub.2                                                                              O  S                                  59   IB                                                                                  ##STR450##      CH.sub.3                                                                          CHF.sub.2                                                                              O  S                                  60   IA                                                                                  ##STR451##      CH.sub.3                                                                          CHF.sub.2                                                                              O  S                                  61   IA                                                                                  ##STR452##      CH.sub.3                                                                          CH.sub.2 CCH                                                                           O  S  114                             62   IA                                                                                  ##STR453##      CH.sub.3                                                                          CH.sub.2 CCH                                                                           O  S  106                             63   IA                                                                                  ##STR454##      CH.sub.3                                                                          CH.sub.2 CHCH.sub.2                                                                    O  S  (amorphous)                     64   IA                                                                                  ##STR455##      CH.sub.3                                                                          CH.sub.2 CHCH.sub.2                                                                    O  S  (amorphous)                     65   IB                                                                                  ##STR456##      CH.sub.3                                                                          CHF.sub.2                                                                              O  S  (amorphous)                     66   IB                                                                                  ##STR457##      CH.sub.3                                                                          CHF.sub.2                                                                              O  S  (amorphous)                     67   IA                                                                                  ##STR458##      CH.sub.3                                                                          CH.sub.3 O  S  (amorphous)                     68   IA                                                                                  ##STR459##      CH.sub.3                                                                          CH.sub.3 O  S  (amorphous)                     69   IB                                                                                  ##STR460##      CH.sub.3                                                                          CHF.sub.2                                                                              O  S                                  70   IB                                                                                  ##STR461##      CH.sub.3                                                                          CHF.sub.2                                                                              O  S                                  71   IA                                                                                  ##STR462##      CH.sub.3                                                                          H        O  S                                  72   IA                                                                                  ##STR463##      CH.sub.3                                                                          H        O  S                                  73   IA                                                                                  ##STR464##      CH.sub.3                                                                          H        O  S                                  __________________________________________________________________________

Starting Materials of the Formula (II): EXAMPLE (II-1) ##STR465## Step 1

A stirred mixture of 12 g (0.12 mol) of calcium carbonate, 150 ml ofwater, 13.7 g (0.12 mol) of thiophosgene and 100 ml of dichloromethaneis treated with 26.4 g (0.12 mol) of 6-amino-7-fluoro-3,4-dihydro-3-oxpropargyl-(2H)-1,4-benzoxazine in 50 ml of dichloromethane. The reactionmixture is stirred for approximately 3 hours at 35 C. to 40 C. Then,after filtration, the organic phase is separated off, dried usingmagnesium sulphate and filtered. The filtrate is freed from solvent invacuo.

This gives 27 g (85.9% of theory) of6-isothiocyanato-7-fluoro-3,4-dihydro-3-oxo-4-propargyl-(2H)-1,4-benzoxazine.Melting point: 128 C.

Step 2

A solution of 5.24 g (20 mMol) of6-isothiocyanato-7-fluoro-3,4-dihydro-3-oxo-4-propargyl-(2H)1,4-benzoxazine in 60 ml of tetrahydrofuran is treated at 5 C. to 10 C.with 0.92 g (20 mMol) of methylhydrazine. After the mixture has beenstirred for two hours at 10 C., the solvent is stripped off in vacuo andthe solid residue is recrystallized from iso-propanol.

This gives 4.7 g (76.3% of theory) of2-methyl-4-(7-fluoro-3,4-dihydro-3-oxo-4-propargyl-(2H)-1,4-benzoxazin-6-yl)-thiosemicarbazide.Melting point: 162 C.

Other examples of compounds of the formula (II)--and/or tautomersthereof--which can be prepared analogously to Example (II-1) are thosegiven in Table 2 below.

                  TABLE 2                                                         ______________________________________                                        Examples of the compounds of the formula (II)                                                                          Melting                              Ex.                                      point                                No.  Ar                 R      R.sup.2                                                                            A    (C.)                                 ______________________________________                                        II-2                                                                                ##STR466##        CH.sub.3                                                                             H    S    173                                  II-3                                                                                ##STR467##        CH.sub.3                                                                             H    S    154                                  II-4                                                                                ##STR468##        CH.sub.3                                                                             H    S    125                                  II-5                                                                                ##STR469##        CH.sub.3                                                                             H    S    (oil)                                II-6                                                                                ##STR470##        CH.sub.3                                                                             H    S    154                                  II-7                                                                                ##STR471##        CH.sub.3                                                                             H    S    111                                  II-8                                                                                ##STR472##        CH.sub.3                                                                             H    S    187                                  II-9                                                                                ##STR473##        CH.sub.3                                                                             H    S    166                                  II-10                                                                               ##STR474##        CH.sub.3                                                                             H    S    116                                  II-11                                                                               ##STR475##        CH.sub.3                                                                             H    S    157                                  II-12                                                                               ##STR476##        CH.sub.3                                                                             H    S    161                                  II-13                                                                               ##STR477##        CH.sub.3                                                                             H    S    152                                  II-14                                                                               ##STR478##        CH.sub.3                                                                             H    S    118                                  II-15                                                                               ##STR479##        H      H    S    164                                  II-16                                                                               ##STR480##        C.sub.2 H.sub.5                                                                      C.sub.2 H.sub.5                                                                    S                                         II-17                                                                               ##STR481##        H      H    S    129                                  II-18                                                                               ##STR482##        H      H    S    240                                  II-19                                                                               ##STR483##        H      H    S                                         ______________________________________                                    

Use Examples EXAMPLE A

Post-emergence test

Solvent: 5 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent, thestated amount of emulsifier is added and the concentrate is diluted withwater to the desired concentration.

Test plants which have a height of 5-15 cm are sprayed with thepreparation of the active compound in such a way as to apply theparticular amounts of active compound desired per unit area. After threeweeks, the degree of damage to the plants is rated in % damage incomparison to the development of the untreated control.

The figures denote:

0%=no action (like untreated control)

100%=total destruction

EXAMPLE B

Pre-emergence test

Solvent: 5 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent, thestated amount of emulsifier is added and the concentrate is diluted withwater to the desired concentration.

Seeds of the test plants are sown in normal soil and, after 24 hours,watered with the preparation of the active compound. It is expedient tokeep constant the amount of water per unit area. The concentration ofthe active compound in the preparation is of no importance, only theamount of active compound applied per unit area being decisive. Afterthree weeks, the degree of damage to the plants is rated in % damage incomparison to the development of the untreated control.

The figures denote:

0%=no action (like untreated control)

100%=total destruction

                                      TABLE A                                     __________________________________________________________________________    Post-emergence test/greenhouse                                                     Rate of                                                                  Active                                                                             application                                                              compound                                                                           g/ha  Wheat                                                                             Abutilon                                                                           Amaranthus                                                                          Datura                                                                            Ipomoea                                                                            Solanum                                                                            Viola                                 __________________________________________________________________________    5    30    10  100  100   100 100  100  100                                   6    30     5   95  100   100 100  100  100                                   2    30    20  100  100   100 100  100  100                                   8    30    20  100  100   100 100  100  100                                   __________________________________________________________________________

                                      TABLE B                                     __________________________________________________________________________    Pre-emergence test/greenhouse                                                      Rate of                                                                  Active                                                                             application                                                              compound                                                                           g/ha  Barley                                                                            Abutilon                                                                           Chenopodium                                                                          Galinsoga                                                                          Matricaria                                                                         Portulaca                                                                          Solanum                             __________________________________________________________________________    5    125   10  100   95     90  100  100  100                                 6     60   20   95  100     80   70   95   95                                 2    125   10  100  100    100  100  100  100                                 8    125   10  100  100    100  100  100  100                                 3    125    0  100  100    100   95  100  100                                 __________________________________________________________________________

We claim:
 1. Substituted aryliminoheterocycles of the general formula (I) ##STR484## in which A represents oxygen or sulphurE represents one of the following groups ##STR485## where Q represents oxygen or sulphur andR² represents hydrogen, cyano, or represents alkyl having 1 to 6 carbon atoms which is optionally substituted by cyano, halogen, C₁ -C₄ -alkoxy, C₁ -C₄ -alkyl-carbonyl or C₁ -C₄ -alkoxy-carbonyl, or represents alkenyl or alkinyl each of which has 2 to 6 carbon atoms and each of which is optionally substituted by halogen, or represents cycloalkyl having 3 to 6 carbon atoms or cycloalkenyl having 5 or 6 carbon atoms, each of which is optionally substituted by halogen or C₁ -C₄ -alkyl, R represents alkyl having 1 to 6 carbon atoms which is optionally substituted by cyano, halogen, C₁ -C₄ -alkoxy, C₁ -C₄ -alkyl-carbonyl or C₁ -C₄ -alkoxy-carbonyl, or represents alkenyl or alkinyl each of which has 2 to 6 carbon atoms and each of which is optionally substituted by halogen, and Ar represents one of the monocyclic or bicyclic aryl or heteroaryl groups below, ##STR486## each of which is optionally substituted, and in which R³ represents hydrogen or halogen,R⁴ represents cyano, nitro, thiocarbamoyl, halogen, or in each case optionally halogen-substituted C₁ -C₄ -alkyl or C₁ -C₄ -alkoxy, R⁵ represents the group below

    --A.sup.1 --A.sup.2 --A.sup.3

in which A¹ represents a single bond, or represents oxygen, sulphur, --SO--, --SO₂ --, --CO-- or the group --N--A⁴ -- where A⁴ represents hydrogen, hydroxyl, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, phenyl, C₁ -C₄ -alkylsulphonyl or phenylsulphonyl or A¹ furthermore represents C₁ -C₆ -alkanediyl, C₂ -C₆ -alkenediyl, C₂ -C₆ -azaalkenediyl, C₂ -C₆ -alklinediyl, C₃ -C₆ -cycloalkanediyl, C₃ -C₆ -cycloalkenediyl or phenylene, each of which is optionally substituted by fluorine, chlorine or bromine, A² represents a single bond, or represents oxygen, sulphur, --SO--, --SO₂ --, --CO-- or the group --N--A⁴ -- where A⁴ represents hydrogen, hydroxyl, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, phenyl, C₁ -C₄ -alkylsulphonyl or phenylsulphonyl or A² furthermore represents C₁ -C₆ -alkanediyl, C₂ -C₆ -alkenediyl, C₂ -C₆ -azaalkenediyl, C₂ -C₆ -alkinediyl, C₃ -C₆ -cycloalkanediyl, C₃ -C₆ -cycloalkenediyl or phenylene, each of which is optionally substituted by fluorine, chlorine or bromine, A³ represents hydrogen, hydroxyl, amino, cyano, isocyano, thiocyanato, nitro, carboxyl, carbamoyl, thiocarbamoyl, sulpho, chlorosulphonyl, halogen, or represents alkyl, alkoxy, alkylthio, alkylsulphonyl, alkylsulphonyl, alkylamino, dialkylamino, alkoxycarbonyl or dialkoxy(thio)phosphoryl, each of which has 1 to 6 carbon atoms in the alkyl groups and each of which is optionally substituted by halogen or C₁ -C₄ -alkoxy, or represents alkenyl, alkenyloxy, alkenylamino, alkylidenamino, alkenyloxycarbonyl, alkinyl, alkinyloxy, alkinylamino or alkinyloxycarbonyl, each of which has 2 to 6 carbon atoms in the alkenyl, alkylidene or alkinyl groups and each of which is optionally substituted by halogen or represents cycloalkyl, cycloalkyloxy, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylidenamino, cycloalkyloxycarbonyl or cycloalkylalkoxy-carbonyl, each of which has 3 to 6 carbon atoms in the cycloalkyl groups and, if appropriate, 1 to 4 carbon atoms in the alkyl groups and each of which is optionally substituted by halogen, cyano, carboxyl, C₁ -C₄ -alkyl and/or C₁ -C₄ -alkoxycarbonyl, or represents phenyl, phenyloxy, phenyl-C₁ -C₄ -alkyl, phenyl-C₁ -C₄ -alkoxy, phenyloxycarbonyl or phenyl-C₁ -C₄ -alkoxycarbonyl, each of which is optionally substituted by nitro, cyano, carboxyl, halogen C₁ -C₄ -alkyl, C₁ -C₄ -halogenoalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -halogenoalkyloxy and/or C₁ -C₄ -alkoxy-carbonyl, (in each case optionally fully or partially hydrogenated) pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, triazinyl, pyrazolyl-C₁ -C₄ -alkyl, furyl-C₁ -C₄ -alkyl, thienyl-C₁ -C₄ -alkyl, oxazolyl-C₁ -C₄ -alkyl, isoxazol-C₁ -C₄ -alkyl, thiazol-C₁ -C₄ -alkyl, pyridinyl-C₁ -C₄ -alkyl, pyrimidinyl-C₁ -C₄ -alkyl, pyrazolylmethoxy, furylmethoxy, or represents perhydropyranylmethoxy or pyridylmethoxy, R⁶ represents hydrogen or halogen, R⁷ represents hydrogen, hydroxyl, or represents alkyl having 1 to 6 carbon atoms which is optionally substituted by cyano, halogen, C₁ -C₄ -alkoxy, C₁ -C₄ -alkyl-carbonyl or C₁ -C₄ -alkoxy-carbonyl, or represents alkenyl or alkinyl, each of which has 2 to 6 carbon atoms and each of which is optionally substituted by halogen, or represents cycloalkyl or cycloalkylalkyl, each of which has 3 to 6 carbon atoms in the cycloalkyl moiety and, if appropriate, 1 to 4 carbon atoms in the alkyl moiety and each of which is optionally substituted by halogen or C₁ -C₄ -alkyl, or represents alkoxy or alkenyloxy, each of which has up to 6 carbon atoms and each of which is optionally substituted by halogen, or represents benzyl or benzyloxy, each of which is optionally substituted by cyano, halogen, C₁ -C₄ -alkyl, C₁ -C₄ -halogenoalkyl, C₁ -C₄ -alkoxy or C₁ -C₄ -halogenoalkoxy, and G represents one of the following groups --O--CO--, --S--CO--, --O--C(R⁸,R⁹)--CO--, --C(R⁸,R⁹)--O--CO--, --C(R⁸,R⁹)--C(R⁸,R⁹)--, --C(R⁸,R⁹)--C(R⁸,R⁹)--CO--, --C(R⁸)═C(R⁸)--, --C(R⁸)═C(R⁸)--CO--, --C(R⁸,R⁹)--CO--, --N(R¹⁰)--C(R⁸,R⁹)--CO--, --C(R⁸)═N--, --O--CO--C(R⁸,R⁹)--where R⁸ and R⁹ are identical or different and individually represent hydrogen or alkyl having 1 to 6 carbon atoms or together represent alkanediyl having 2 to 6 carbon atoms, and R¹⁰ represents hydrogen or alkyl having 1 to 6 carbon atoms.
 2. Substituted aryliminoheterocycles of the general formula (I) according to claim 1, in whichA represents oxygen or sulphur, E represents one of the following groups ##STR487## where Q represents oxygen or sulphur andR² represents hydrogen, cyano, or represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, each of which is optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, acetyl, propionyl, methoxycarbonyl or ethoxycarbonyl, or represents propenyl, butenyl, propinyl or butinyl, each of which is optionally substituted by fluorine, chlorine or bromine, or represents cyclopentenyl or cyclohexenyl, R represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, each of which is optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, acetyl, propionyl, methoxycarbonyl or ethoxycarbonyl, or represents propenyl, butenyl, propinyl or butinyl, each of which is optionally substituted by fluorine, chlorine or bromine, and Ar represents one of the monocyclic or bicyclic aryl or heteroaryl groups below, ##STR488## each of which is optionally substituted, in which R³ represents hydrogen, fluorine or chlorine,R⁴ represents cyano, chlorine, bromine, methyl or trifluoromethyl, R⁵ represents the group below

    --A.sup.1 --A.sup.2 --A.sup.3

in which A¹ represents a single bond, or represents oxygen, sulphur, --SO--, --SO₂ --, --CO-- or the group --N--A⁴ -- where A⁴ represents hydrogen, hydroxyl, methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylsulphonyl or ethylsulphonyl, or A¹ furthermore represents methylene, ethane-1,1-diyl, ethane-1,2-diyl, propane-1,1-diyl, propane-1-2-diyl, propane-1-3-diyl, ethene-1,2diyl, propene-1,2-diyl, propene-1-3-diyl, ethine-1,2-diyl or propine-1-3-diyl, A² represents a single bond, or represents oxygen, sulphur, --SO--, --SO₂ --, --CO-- or the group --N--A⁴ -- where A⁴ represents hydrogen, hydroxyl, methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl or phenylsulphonyl, or A² furthermore represents methylene, ethane-1,1-diyl, ethane-1,2diyl, propane-1,1-diyl, propane-1-2-diyl, propane-1-3-diyl, ethene-1,2-diyl, propene-1,2-diyl, propene-1-3-diyl, ethine-1,2-diyl, propine-1,2-diyl or propine-1-3-diyl, A³ represents hydrogen, hydroxyl, amino, cyano, nitro, carboxyl, carbamoyl, sulpho, fluorine, chlorine, bromine, or represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-, i-, s- or t-pentyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, n-, i-, s- or t-pentyloxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl, methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino, diethylamino, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, dimethoxyphosphoryl, diethoxyphosphoryl, dipropoxyphosphoryl or diisopropoxy-phosphoryl, each of which is optionally substituted by fluorine, chlorine, methoxy or ethoxy, or represents propenyl, butenyl, propenyloxy, butenyloxy, propenylamino, butenylamino, propylidenamino, butylidenamino, propenyloxycarbonyl, butenyloxycarbonyl, propinyl, butinyl, propinyloxy, butinyloxy, propinylamino, butinylamino, propinyloxycarbonyl or butinyloxycarbonyl, each of which is optionally substituted by fluorine or chlorine, or represents cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclo-pentyloxy, cyclohexyloxy, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclo-propylmethoxy, cyclo-butylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, cyclopentylidenamino, cyclohexylidenamino, cyclopentyloxy-carbonyl, cyclohexyloxycarbonyl, cyclopentylmethoxycarbonyl or cyclohexylmethoxycarbonyl, each of which is optionally substituted by fluorine, chlorine, cyano, carboxyl, methyl, ethyl, n- or i-propyl, methoxycarbonyl or ethoxycarbonyl, or represents phenyl, phenyloxy, benzyl, phenylethyl, benzyloxy, phenyloxycarbonyl, benzyloxycarbonyl, (in each case optionally fully or partially hydrogenated) pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, triazinyl, pyrazolylmethyl, furylmethyl, thienylmethyl, oxazolylmethyl, isoxazolmethyl, thiazolmethyl, pyridinylmethyl, pyrimidinylmethyl, pyrazolylmethoxy, furylmethoxy or pyridylmethoxy, each of which is optionally substituted by nitro, cyano, carboxyl, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methoxycarbonyl and/or ethoxycarbonyl, R⁶ represents hydrogen, fluorine or chlorine, R⁷ represents hydrogen, hydroxyl, or represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, each of which is optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, acetyl, propionyl, methoxycarbonyl or ethoxycarbonyl, or represents propenyl, butenyl, propinyl or butinyl, each of which is optionally substituted by fluorine, chlorine or bromine, or represents cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, each of which is optionally substituted by fluorine, chlorine, bromine, methyl or ethyl, or represents methoxy, ethoxy, n- or i-propoxy, n-, i- or s-butoxy, propenyloxy or butenyloxy, each of which is optionally substituted by fluorine and/or chlorine, or represents benzyl or benzyloxy, each of which is optionally substituted by cyano, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy or trifluoromethoxy, and G represents one of the following groups --O--CO--, --S--CO--, --O--C(R⁸,R⁹)--CO--, --C(R⁸,R⁹)--O--CO--, --C(R⁸,R⁹)--C(R⁸,R⁹)--, --C(R⁸)═C(R⁸)--, --C(R⁸,R⁹)--CO--, --N(R¹⁰)--C(R⁸,R⁹)--CO--, --C(R⁸)═N--, --O--CO--C(R⁸,R⁹)--where R⁸ and R⁹ are identical or different and individually represent hydrogen, methyl, ethyl, n- or i-propyl or together represent ethane-1,2-diyl, and R¹⁰ represents hydrogen, methyl, ethyl, n- or i-propyl.
 3. Process for the preparation of substituted aryliminoheterocycles of the general formula (I) ##STR489## in which A, E, R and Ar have the meanings given in claim 1, characterized in that arylimino compounds of the general formula (II) ##STR490## in which A, R, R² and Ar have the abovementioned meanings--and compounds which are tautomeric to these--are cyclized with reactive carbonic acid derivatives of the general formula (III) ##STR491## in which Q has the abovementioned meaning andX represents halogen, alkoxy, aryloxy or aralkoxy,if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent, and, if appropriate, the resulting compounds of the formulae (IA) and (IB), in the event that R² in these formulae is hydrogen, are reacted with alkylating agents of the general formula (IV)

    R.sup.2 --X.sup.1                                          (IV)

in which R² has the abovementioned meaning with the exception of hydrogen and X¹ represents halogen or the group --O--SO₂ --O--R²,if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent.
 4. A method of controlling unwanted vegetation which comprises applying to such vegetation or to a locus from which it is desired to exclude such vegetation a herbicidally effective amount of a compound according to claim
 1. 5. A herbicidal composition comprising a herbicidally effective amount of a compound according to claim 1 and a surfactant. 